180776-30-1

Upstream product

• 180776-27-6 (3aS,8aR)-3-[(S)-2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-pent-4-enoyl]-3,3a,8,8a-tetrahydro-indeno[1,2-d]oxazol-2-one 
• 180776-26-5 (3aS,8aR)-3-[3-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionyl]-3,3a,8,8a-tetrahydro-indeno[1,2-d]oxazol-2-one 
• 180776-28-7 (S)-2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-pent-4-enoic acid 
• 180776-47-0 3-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid ethyl ester 
• 180776-25-4 3-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid 
• 131121-18-1 (E)-ethyl 3-((3aR,4R,6R,6aR)-tetrahydro-4-methoxy-2,2-dimethylfuro[3,4-d][1,3]dioxol-6-yl)acrylate 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 532-20-7 D-Ribose 
• 33985-40-9 (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 
• 100-39-0 benzyl bromide 
• 180776-29-8 [(S)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-but-3-enyl]-carbamic acid benzyl ester 

Downstream Products

• 262423-15-4 Methyl 6-[benzyl(benzyloxycarbonyl)amino]-5,7-dideoxy-2,3-O-isopropylidene-α-L-talo-octofuranoside 
• 1403482-56-3 C₃₈H₄₆N₂O₁₀ 
• 1431134-81-4 C₃₀H₄₀N₂O₈ 
• 1403482-52-9 C₃₆H₄₉N₃O₈ 
• 1403482-48-3 C₂₇H₃₄INO₆ 
• 1431134-96-1 C₃₉H₄₆N₂O₁₀ 

Relevant academic research and scientific papers

COFACTOR ANALOGS AS METHYLTRANSFERASE INHIBITORS FOR TREATING CANCER

Compounds having methyltransferase inhibitory activity are disclosed. The compounds have the structure (I) They are useful in the treatment of cancer and similar diseases associated with inappropriate methyltransferase activity.

METHYLTRANSFERASE INHIBITORS FOR TREATING CANCER

Compounds having methyltransferase inhibitory activity are disclosed. The compounds are amino acids, esters and amides having a common core based on adenosine or deazaadenosine and are useful in the treatment of cancer and similar diseases associated with inappropriate methyltransferase activity.

Sinefungin derivatives as inhibitors and structure probes of protein lysine methyltransferase SETD2

Epigenetic regulation is involved in numerous physiological and pathogenic processes. Among the key regulators that orchestrate epigenetic signaling are over 50 human protein lysine methyltransferases (PKMTs). Interrogation of the functions of individual PKMTs can be facilitated by target-specific PKMT inhibitors. Given the emerging need for such small molecules, we envisioned an approach to identify target-specific methyltransferase inhibitors by screening privileged small-molecule scaffolds against diverse methyltransferases. In this work, we demonstrated the feasibility of such an approach by identifying the inhibitors of SETD2. N-propyl sinefungin (Pr-SNF) was shown to interact preferentially with SETD2 by matching the distinct transition-state features of SETD2's catalytically active conformer. With Pr-SNF as a structure probe, we further revealed the dual roles of SETD2's post-SET loop in regulating substrate access through a distinct topological reconfiguration. Privileged sinefungin scaffolds are expected to have broad use as structure and chemical probes of methyltransferases.

Total synthesis of (+)-sinefungin

Sinefungin (1) a nucleoside antibiotic isolated from Streptomyces has been synthesized from D-ribose. Both the C-6 and C-9 stereogenic centers were constructed by efficient asymmetric syntheses. The C-6 amine stereochemistry was set by a highly diastereoselective allylation (> 99% de) of a (1S,2R)-1-amino-2-indanol-derived oxazolidinone 9 followed by a Curtius rearrangement of 11 to 12. The C-9 amino acid stereochemistry of sinefungin (1) was established by a rhodium chiral bisphosphine-catalyzed asymmetric hydrogenation of an α-(acylamino)acrylate derivative. The anomeric adenosylation of the mixture of anomeric acetates 20 in the presence of C-6 urethane NH was found to be extremely difficult. Conversion of the C-6 urethane NH as its N-benzyl derivative 21 was necessary prior to the adenosylation reaction. Successful adenosylation was effectively carried out by Vorbruggen's protocol utilizing persilylated N6-benzoyladenine and trimethylsilyl triflate.